Lainey Wilson, Trisha Yearwood Discuss Early Country Radio Struggles & Advice From Dolly Parton During Country Radio Seminar

On Thursday (Feb. 29), three-time Grammy winner Trisha Yearwood led a conversation with reigning CMA entertainer of the year Lainey Wilson, as part of the 2024 Country Radio Seminar in downtown Nashville.

Among the topics they discussed were the importance of women artists standing up for themselves, the similarities in their respective career paths, and battling imposter syndrome.

Both have carved out multi-faceted careers, with No. 1 Billboard Country Airplay hits, awards accolades and work in television. (Wilson was featured on the series Yellowstone, while Yearwood is known for her Food Network cooking series Trisha’s Southern Kitchen, as well as roles in Dr. Quinn, Medicine Woman, the live television musical The Passion and a recurring role on the military drama JAG).

In May 1991, Yearwood’s debut single “She’s in Love With the Boy” appeared on the Country Airplay chart; by early August that same year, it had reached the pinnacle. In 2021, Wilson earned her first No. 1 Billboard Country Airplay hit with “Things a Man Oughta Know,” and has followed with a string of chart-toppers.

They discussed their rapid career rises, with Yearwood recalling that time period surrounding the radio success for her debut radio single, “She’s in Love With the Boy” feeling like “a dream come true,” but she also described it as “holding onto a runaway train and just trying to keep up. And a lot of it is a blur, until I made myself figure out how to be in the moment.”

“I’m in the process of that right now… the last few years have been a whirlwind in the best kind of way,” Wilson responded, adding, “Somebody was telling me — I think it was back in 2017 when I signed my first publishing deal — they told me, ‘It’s going to feel like you’re being drug behind a ski boat for years.’”

Taking on country radio

Wilson (who earned her first Grammy this year for her album Bell Bottom Country) has earned four No. 1 Country Airplay hits: “Things a Man Oughta Know,” the Jelly Roll collaboration “Save Me,” the two-week chart-topper “Never Say Never” (with Cole Swindell) and the three-week solo No. 1, “Watermelon Moonshine.”

But Wilson recalled how when she was first taking her music to radio, there was at least one difficult encounter with a radio exec, pointing out the importance of not taking no for an answer.

“Radio tour, it was hard. It was really, really hard, I’m not going to lie to y’all,” Wilson said. “It taught me a lot. I made a lot of friends along the way that I still text and we talk all the time. But I do remember one specific stop: I go in and we waited in the foyer. He brings us into his office and he said, ‘Play me what you got.’ This was my first single, ‘Dirty Looks.’ He said, ‘You should have left your guitar in the car. I don’t want to hear you play. I want to hear what it sounds like through the speakers.’ Well, he had like 1997 computer speakers, so of course you couldn’t understand anything that the song was saying. He listened to it twice, back-to-back. I was just sitting there and he let the second time finish. He leans across his desk and he said, ‘Lainey, you’re just not that good.’ And I leaned across his desk and I said, ‘So-and-so, out of the 10 years that I’ve been in Nashville, you telling me that don’t mean s–t.’”

She went on to add, “It did light another fire underneath me. After I left there, I was like, ‘Okay, at the end of the day you put yourself out there. Not everybody’s going to like you or love you … I think moments like that, they’re not fun. But if anything, they do build character. They give you fun stories to talk about with Trisha Yearwood.”

Yearwood, who has earned five No. 1 Country Airplay hits, offered up her own difficult encounter during one radio interview, when a radio interviewer brought up a fake story about Yearwood that had been in a tabloid.

“I was doing a show and went to the radio station that was sponsoring the show,” Yearwood recalled. “The DJ thought it was funny..and said, ‘Let’s talk about this.’ I said, ‘I can’t believe you would ask me that question.’ And I left, and I’ve never done anything like that.” She went on to add that, “They were very apologetic, but to say to you — and I don’t know if you’ve had that experience yet — but I wish I had learned earlier. I was about your age that I was like, ‘I’m kind and I’m nice, but there’s some things that aren’t okay.’ It’s okay to say that’s not right.”

Leading with purpose — and advice from Dolly

Yearwood also noted the importance of being selective in the projects you agree to take on, to make sure they are in alignment with an artist’s goals.

“I never said, ‘I want to have a cookbook. I want to have a cooking show,’” Yearwood said. “But I was open for the opportunities when they came. And I’ve said no to a lot more stuff than I said yes to. But I say yes to the things that feel right to me. And that’s always the bar to follow. People can read through things when they know it’s not genuine.”

“There’s definitely been times where I felt like I was doing it all,” Wilson said, relating some advice she received from Dolly Parton. “I asked her, ‘How do you decide everything that you’re doing?’ She said, ‘It has to be something that I’m really passionate about and excited to do. It that’s not the case, then I don’t do it.’”

Navigating Social Media

Wilson also shared advice she wrote down shortly after meeting Yearwood for the first time. “She said, ‘For y’all right now, the line between being loved and hated by the world is getting smaller every day. I was like, ‘Oh, Lord’ — because sometimes people love you, people hate you, and then sometimes people hate you because people love you.”

“That’s true: There’s this whole thing of everybody rooting [for you], then when you get to the top of the heap, now we got to figure out a way to make her not superhuman. Now we got to take her down a peg,” Yearwood said. “I guess that’s human nature and the social media aspect makes the world bigger, and smaller.”

She added, “Every time I used to read the comments — good God, don’t do that. I used to read and I’d just get so upset by things and I would call my people and go, ‘We’re getting off of social media.’ And they were like, ‘Actually, you can’t really do that.’ I wanted to interact, but then I realized that I also needed to protect my mental health.”

“Yeah, because even if you put your eyes on it for a split second, it still pings your heart … you’re still human.”

Battling Imposter Syndrome

They also fielded questions from the audience, including one about staying centered as a person during a career rise, and battling imposter syndrome.

“I have a lot of people in my life who remind me of my hard work,” Wilson said. “Even folks like Luke Combs. The day after the CMAs, he texted me this huge novel, and he’s like, ‘Lainey, I just want you to remember that you’re that girl that moved here and lived in that camper trailer and I knew you back then. I’m so proud to see your hard work being recognized and don’t you start thinking that you didn’t deserve this for one second.’ It’s keeping people like those close people who lift you up — also just talking to the Lord. At the end of the day, I got to keep those things close really, really close because this business is hard.”